Table 3.
Geometry of intra- and intermolecular hydrogen bonds for 4a–d.
| Compounds | D–H∙∙∙A | d(D–H) | d(H···A) | d(D···A) | <(D–H···A) |
|---|---|---|---|---|---|
| 4a | N4–H4···N5 | 0.95 (2) | 1.87 (2) | 2.692 (2) | 143 (2) |
| C46–H46···N3 | 0.95 | 2.26 | 2.825 (3) | 117.3 | |
| C56–H56···F4 i | 0.95 | 2.66 | 3.592 (3) | 168.8 | |
| C61–H613···F4 i | 0.98 | 2.66 | 3.372 (2) | 129.6 | |
| 4b | N4–H4···N5 | 0.86 (2) | 1.93 (2) | 2.669 (2) | 143 (2) |
| C45–H45···Cl5 i | 0.95 | 2.80 | 3.591 (2) | 141.2 | |
| C46–H46···N3 | 0.95 | 2.35 | 2.951 (3) | 120.9 | |
| C61–H611···F4 ii | 0.98 | 2.61 | 3.280 (2) | 125.5 | |
| C61–H613···Cl5 iii | 0.98 | 2.92 | 3.738 (2) | 141.8 | |
| 4c | N4A–H4A···N5A | 0.90 (3) | 1.86 (3) | 2.678 (4) | 151 (3) |
| N4B–H4B···N5B | 0.88 (4) | 1.84 (4) | 2.651 (4) | 152 (3) | |
| C42A–H42A···O5A | 0.95 | 2.66 | 3.552 (12) | 156.5 | |
| C42C–H42C···O5A | 0.95 | 2.73 | 3.577 (13) | 149.4 | |
| C42B–H42B···O5B | 0.95 | 2.56 | 3.374 (8) | 144.4 | |
| C46A–H46A···N3A | 0.95 | 2.36 | 2.935 (12) | 118.6 | |
| C46C–H46C···N3A | 0.95 | 2.30 | 2.868 (12) | 118.1 | |
| C46B–H46B···N3B | 0.95 | 2.52 | 3.060 (9) | 115.9 | |
| C46D–H46D···N3B | 0.95 | 2.19 | 2.765 (9) | 117.8 | |
| C43B–H43B···F4B i | 0.95 | 2.03 | 2.643 (10) | 121.0 | |
| C58A–H5A3···N4A ii | 0.98 | 2.77 | 3.283 (5) | 113.6 | |
| C58D–H5D2···N4B ii | 0.98 | 2.66 | 3.241 (10) | 118.4 | |
| C61A–H6A1···F4D iii | 0.98 | 2.61 | 3.336 (8) | 131.1 | |
| C61A–H6A3···F4D iv | 0.98 | 2.59 | 3.381 (8) | 137.4 | |
| 4d | N4–H4···N5 | 0.87 (2) | 1.90 (2) | 2.651 (2) | 144.1 (18) |
| C46–H46···N3 | 0.95 | 2.35 | 2.933 (2) | 119.3 | |
| C55–H55···F52 i | 0.95 | 2.47 | 3.394 (2) | 162.8 | |
| C52–H52···F4 ii | 0.95 | 2.82 | 3.280 (2) | 111.0 |
Symmetry codes: 4a: (i) −x+3/2, y−1/2, z+1/2; 4b: (i) −x+3/2, −y, z−1/2; (ii) x, y+1, z; (iii) −x+3/2, −y+1, z−1/2; 4c: (i) −x+1, y, −z+3/2; (ii) x, y−1, z; (iii) x, −y+2, z−1/2; (iv) x, −y+1, z−1/2; 4d: (i) −x+1, y+1/2, −z+1/2; (ii) x, y−1, z.